Today I’m doing something a little different! Instead of my usual trends and insights, I’m sharing a clip from my recent guest appearance on Scot Wingo’s podcast, Retailgentech. Scott flipped the script and let me ask him about his career journey, his perspective on where retail is headed, and one of the biggest questions in e-commerce right now: How will large language models (LLMs) like ChatGPT make their money in the future?

Will they follow the traditional ad-based route we’ve seen from Google and Facebook? Or will they build marketplaces and take a cut from transactions, as we’re starting to see with new initiatives from Walmart, Instacart, and DoorDash?

In this conversation, we dive into how AI-driven commerce could reshape loyalty, customer ownership, and what it means to be a “merchant of record” in the next era of retail. Find the link to the full Retailgentic podcast below under 'Links & Resources'.

This episode is sponsored by Connected Commerce at Acosta Group

Timeline

[1:01] – Will LLMs make money through ads, or through marketplaces?
[1:30] – Scot breaks down ChatGPT’s “checkout” model and why he views it as a marketplace, not an affiliate system.
[2:50] – How Google’s AI agent checkout experience compares and what that means for merchants.
[3:00] – The retailer concern: will AI intermediaries cause commoditization?
[4:00] – Why Scott believes this new wave of AI players won’t repeat the mistakes of Facebook–Google–Amazon.
[6:00] – What it means for retailers to be the “merchant of record” and how that unlocks loyalty opportunities.
[7:30] – The comeback of loyalty programs and non-price differentiators in retail.
[8:30] – How omnichannel experiences and brand identity will help retailers stay relevant in the AI-driven marketplace era.
[9:00] – Wrapping up: why the fundamentals of loyalty, differentiation, and customer connection still matter more than ever.

Links & Resources

• Listen to the full October 14, 2025 Retailgentic episode, Turning the Tables: Kiri Masters Interviews Scot Wingo on Agentic Commerce & AI Shopping
• Subscribe to Retailgentic
• Read my article The 3 Ways Agentic Commerce Could Destroy Retail Media
• Read my article Agentic Shopping Might Seem Crazy. So Did Self-Service Supermarkets.
• Follow Scot Wingo on LinkedIn
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri on LinkedIn